THE OMNI SHOW

Robert Pope: If you want to make sure a project is moving forward on multiple fronts, it's okay to have multiple projects in OmniFocus that relate to that same thing. If you want to wrap them in a folder, you can. But at least that way, that gets you thinking, okay, is this project moving forward on all fronts? And that let's you leverage OmniFocus' next available task type of thing.

Andrew J. Mason: You're listening to The Omni Show, where we connect with the amazing community surrounding The Omni Group's award-winning products. My name's Andrew J. Mason, and today, we learned how Robert Pope uses OmniFocus. Welcome everyone to this episode of The Omni Show. Today, we are thrilled to be able to have Robert Pope with us. Robert Pope has been the Online Learning Consortium's IT director and director of technical operations for over 14 years, and happens to be an avid user of OmniFocus. Robert, we're thrilled to be able to chat with you and get to learn more about you.

Robert Pope: Great. I'm glad to be here.

Andrew J. Mason: Talk to us more about yourself. Where do you find yourself? How do you introduce yourself to people? What are some fun facts about you? How can we get to know you better?

Robert Pope: As you already mentioned, I've been doing this for a little while. I started out as a developer, and before the Online Learning Consortium, I was a freelance developer as well. I started using OmniFocus in my freelance practice, and I enjoy all sorts of methodologies and approaching projects, and I keep finding myself coming back to OmniFocus time and time again. I'm a bit of a Lord of the Rings fan and the D&D stuff, but for the most part, I've found that the OmniFocus community is a great community. There's a lot of integration, you would say, with how OmniFocus works with GTD. I'm also a huge fan of GTD, Getting Things Done, by David Allen. I just have not found a tool that integrates that as well as OmniFocus does.

Andrew J. Mason: Very cool. And talk to us more about the Online Learning Consortium as well, 14 years is quite the career already. What is the Online Learning Consortium, and what do you do there?

Robert Pope: The Online Learning Consortium is a global community of online educators, and we provide resources, conferences, professional development opportunities, for our members, mostly in the higher ed and K-through-12 space, and that's pretty much what we do. It gives me a wide variety of things to work on, from development platforms to conference preparation, call for papers, things like that. So there's a wide variety of things, I'm definitely a technical generalist.

Andrew J. Mason: So almost a human Swiss Army knife there, a lot of different things that you find yourself involved in. And how did you first find out about either The Omni Group or OmniFocus?

Robert Pope: I'm trying to remember what devices I had, but I'm pretty sure OmniFocus was one of the recommended apps in the App Store at the time, I'm an Apple fan. That was my first bit, getting into GTD and looking for software tools that would do it, OmniFocus at the time was really geared towards that. So I would say that GTD was probably my gateway drug into OmniFocus.

Andrew J. Mason: My first interaction with you was in LinkedIn. I saw you had made a post about building a custom ta-da list, it's called, instead of to-do list, where you've built a perspective that looks back over the last couple of weeks and shows what you have accomplished. And I thought, man, that's so important, we don't spend nearly enough time celebrating and being thankful for the things that we did accomplish, and sometimes the tendency is always to be future-looking or forward-looking. When it comes to a first workflow tip for people, where do you head? What words of advice or wisdom do you happen to have for people as just that first step to get started in project management or OmniFocus?

Robert Pope: OmniFocus, when you use it as a hub where you're dumping in everything, because I use it professionally and personally, I always have this idea of a fountain, and I apply this in OmniFocus, but I also apply it in Jira, and we do use Jira for project management for where collaboration is involved. But the idea of putting in a pump, if you have a lot of tasks in there, a lot of them are going to start to get stagnant on you, and just like your pond is going to get nasty and stuff like that, if you put a pump where you're regularly reviewing and looking at the projects, that is really helpful. That's one of the reasons I like the GTD, where you have the weekly review so you're at least surfacing things, but having some sort of practice where you're surfacing old stuff and then being clear, yeah, I'm deferring that next month, next week, whatever, or just not going to do that, communicate with the stakeholder that that's not something that you can do at this time.

Andrew J. Mason: Yeah. And everybody loves that feeling of the first time it really works for you, where you weren't naturally thinking of the thing, the task, the project, and it reminds you, and you're like, man, this is making me look better than I actually am, I see where this is bearing fruit for me, that's very cool. Do you have any tips or tricks for somebody who notices that, man, I am getting more to do in my life than I really know how to handle or what to do with, any first steps into project management or task management, what's your go-to advice in that space?

Robert Pope: Get comfortable managing a project in Word and Excel, go down to the bare basics and get good at that. If you don't have the basics under your belt, the tools can get to be pretty overwhelming. And then, once you pick a tool, once you start, say, doing OmniFocus, or if you pick a methodology like GTD, you've got to stick with it long enough so that you start to see the patterns. And then, you need to make sure that you build into your process some sort of feedback loop so you can continually improve it. So one of the things that I've done is I recommend people start with the GTD course on LinkedIn Learning, for example. They might not have OmniFocus and they might start off with using Google Tasks or something like that to organize their stuff and reviewing them once a week, or just some sort of simple tool, but then later on, I think as they get the methodologies down and start the patterns, that's when the tools like OmniFocus really start to shine.

Andrew J. Mason: I want to call out and dig a little bit deeper on that phrase you just used, looked for patterns. What do you mean when you say look for patterns, and what do you suggest people do as they look for the patterns that happen to emerge in their lives?

Robert Pope: One of the daily practices that I have is journaling, and at the end of the week, I go and reread the entries from the previous week, and at the end of the month, I read my weekly summaries to help with that. But a really simple example at a micro level is if you have a task you're marked as, say, reoccurring, it comes up every day, every week, or every month, take that little bit of extra time to make doing that task as smooth as possible. So just a super basic example, you might have a task that says, "Check the system logs in system X" type of thing. Okay, great. Use the notes in OmniFocus to have a link directly to that, so that way, you don't have to go find it every time you do it. And if you take the time to have those reoccurring tasks really streamlined, and you have your notes in there so you can go right to it, it keeps you in flow so you don't break out of it. If there's anything that you're doing, where in your mind, it's like, oh man, this is so annoying, I tell people, you've got to put on your diva hat, where if you're doing something and there's anything in your process that would trigger you as a diva, it's like, no, we're going to fix that right now. Because I imagine, okay, what if I was stuck with this for the next three years? Well, it's only 30 seconds. Yeah, for the next three years, I get to be annoyed for 30 seconds every day. No, thank you.

Andrew J. Mason: That's really good. I don't know what the stats are, but I remember coming across the things on LinkedIn that give you the cumulative, here's how much time we spend over our lifetime just doing things like searching for keys or looking for that lost thing in our wallet or whatever, and how maddening it would be if we experienced all of that at once, so why not optimize for not having that happen again for ourselves? It makes absolute sense. You mentioned using OmniFocus for work and for some personal life stuff, talk to me about where it sits in all of your software. What are the inputs into it and what are some of the exports out of it? What does it look like as information in your day-to-day start to flow through OmniFocus?

Robert Pope: Well, OmniFocus is kind of like my personal task hub, so I tend to have more things flowing into it than out of it. One of the things that I'd like to see, and I noticed The Omni Group starting to entertain chatter in this regard that I'm excited for, is leveraging AI inside of OmniFocus. So not to auto-complete or clarify my tasks, but to identify overall patterns in the task, to recognize, oh, you know what, if you group these tasks together that might be better because you're in the same head space, and provide those kinds of recommendations. But it is the hub. When I get in, literally first thing I do is look at my forecast in OmniFocus. There's this book, I'm trying to remember who wrote it, but in addition to GTD, I'm a big fan of Tiago Forte's Building a Second Brain and the Parrot Method, and I do leverage some of his frameworks in OmniFocus as well, as far as projects and areas and how I organize my thinking there. I know David Allen recommends make sure each project has an actionable task. If you want to make sure a project is moving forward on multiple fronts, it's okay to have multiple projects in OmniFocus that relate to that same thing, if you want to wrap them in a folder, you can. But at least that way, that gets you thinking, okay, is this project moving forward on all fronts? And that let you leverage OmniFocus' next available task type of thing, and move priority projects forward faster because they have a bigger bandwidth in your queue. And then also, I think it's thinking outside the mind, literally using your environment to do some of that cognitive thinking for you so you don't have to do it. So one of the things that I do in my perspective list is I have my perspectives, and I'm looking at them now, but they're organized intentionally to remind me this is what I do first, this is what I do second, this is what I do third. I do the same thing with my bookmarks in Chrome. If I tend to check my email first, that's my first bookmark, my calendar is my second bookmark just to take away... Because weekly is when you're planning, the rest of the time, I don't want to be thinking about what to do, I want to be doing it. So anything I can do to get that thinking out into my environment and out of my head, I try to do.

Andrew J. Mason: Such good words of wisdom there. Even optimizing for what's considered to be the little things, those little things add up, and removing just the one decision of where do I look for the information that's important to me in OmniFocus, saying, "I've built out these perspectives and I can just look at them sequentially, and as long as I tab down them, I know that I've looked at everything I really need to look at," that's excellent advice. And the part about critical paths as well, where you're looking at multiple things that need to be moving inside of a single project, and sometimes it's not just one thing and we forget that, so we're just waiting around for something to happen when we could be moving other portions of a project. That's really, really wise. What about any mistakes that you've made with your system? You look back, you thought it was a good idea, and then now it's like, ah, it didn't work out for me. It might work out for you, but not for me. And maybe people can take it as something that's instructional if they're thinking about doing it this particular way.

Robert Pope: You know how you can get an extreme amount of task overwhelm because you're putting so much in there? I think a lot of times, a mistake is you don't push through... Are you familiar with Barbara Oakley's work?

Andrew J. Mason: Barbara? No, I'm not, I'm not familiar with her.

Robert Pope: She wrote one of the biggest popular online courses, I think it's on Coursera, about learning how to learn. And when I think back on it, it's kind of funny, because some things that I think, oh, that was a mistake, now I kind of recognize that, oh, that was part of the process. Earlier on, I would be like, it's probably a mistake to load as much as, say, you load into OmniFocus, because you're going to get overwhelmed, and I know David Allen is very quick to say, "Get things out of your head, get them in the inbox so you don't have to worry about them." One of the things Tiago points out is when you're writing notes to yourself like that, you're writing to your future self, so that note has to survive the trip into the future. So one of the things is if you're making to-do lists and you're making notes for yourself in a tool like this, you need to make sure that it's going to survive the trip, put enough context in your notes to make sure that it's going to survive that trip, so a week later, you're not like, what the heck was I talking about? Would be one of them. But when you're getting into it and you're just dumping stuff in there, it's like, oh man, there's a lot of stuff, this is back to Barbara Oakley, you have so many mental slots that you can hold onto something, and in the beginning, you might have hundreds and hundreds of tasks, and it's like, oh, there's just so much. But what your brain's going to start doing, if you stick with it and you start recognizing the pattern, you build that feedback loop, is your brain's going to start chunking those. For example, you might start off having 15 things that are separate tasks in a project called morning routine, or something like that, but as you start establishing the habit, and as a cognitive load of making sure you're getting through the morning routine the way you want starts chunking, you're going to realize, oh, I can just have morning routine and I can have in my notes what it is, and you don't have to have all that details and individual task, you'll start noticing your tasks are more cognitively complex, because you started chunking those down a little bit. It's okay if there's a lot, it might seem kind of silly when you're going through and you're checking off two dozen things, but the next time you do your weekly review and that feels excessive, start chunking it down. You might chunk them into groups at first and have three or four groups, and then eventually they might be consumed by the notes, and then there's three things with a few notes, and then eventually it's just the one thing.

Andrew J. Mason: I think that is kind of the ultimate form of automation, where you do need to be discreet at first, thinking about when this works at its best, here are all the individual pieces and parts that need to be moving in the right direction. I always use the example of brushing my kids' teeth when I'm a parent of three and sleep's at a premium, and I don't think there's any shame in that. For some folks that really need to have those discreet things in order to get the pressure off of their brain about having to remember it and knowing that they can rely on a system like OmniFocus to be able to do that for them, it makes sense. And then, over time, you do chunk it into something that's a bigger group of tasks that just becomes one unit for you, so you don't have to sit there and think about each little individual element because it happens by default. But there are times where it's critical, I want the brain surgeon to look at the checklist just in case, even if he's done it 100 times. It makes sense to me.

Robert Pope: You kind of need it out of your head so you can work on it. You can't work on the work in your head, you have to get the work out of your head, and then you can work on how you're working.

Andrew J. Mason: And I do want to call out, again, just for everybody listening, what Robert's saying, this is how a great checklist gets built. David Allen always talks about a checklist being built on negative feedback, if you use those iterations to build nuances into the checklist that already exists, you're going to get better. Just makes sense. Why not do it that way?

Robert Pope: Speaking of game changers though, you had asked about the integration piece in my journey, when I first started, OmniFocus did not have a lot of the features that it has now, and honestly, it was a little bit complicated to do some of the automations. There's tons of stuff you could do with AppleScript, so grateful that's in there. One of the things, and I'm thankful that they have the tablet app and the phone app and the desktop app, and they all play nice together, and a lot of work has gone into making sure that they play nice together, and I really enjoy the interface, when they have got the online web version, in a way, that was a bit of a game changer for me, because you started having automation tools, for example, like Zapier can tie into it, so that's an example. I had mentioned Jira before. Whenever I have a service desk ticket come in, it automatically pops up in my Jira inbox so I can process it that way, all linked up and good to go. That was something that I could not do before, and I did take a foray into other tools for a while, looking at Todoist, like, how can I find a tool that will do what I need to do? But I just keep coming back. In a way, for me, OmniFocus just feels like home now.

Andrew J. Mason: That's fabulous. And Robert, if folks are interested in hanging out with you or entering your orbit and seeing what you're up to or what you're doing these days, how can they do that, how can they connect with you?

Robert Pope: Hit me up on LinkedIn is probably the best way to do it. Is that something that you can provide in the show notes?

Andrew J. Mason: Yeah, we can absolutely put those in the show notes. Robert, thank you again. I just appreciate your willingness to do this. Just so folks know, Robert mentioned this was his first time on a podcast. I feel like you've done phenomenal for that, so you need to keep doing that as well. And there's something about where somebody's not sitting in an ivory tower, just pontificating on, here are my exact tips that I think will improve your life. And this is just an everyday person saying, "Hey, I'm productive, and OmniFocus happens to be the software I'm using to get it done, and here's how I do it." It makes it more accessible. So thank you for joining us, I really appreciate it.

Robert Pope: Thank you, Andrew.

Andrew J. Mason: Hey, and thank all of you for listening today too. You can find us on Mastodon at The Omni Show, at omnigroup.com, you can also find out everything that's happening with The Omni Group at omnigroup.com/blog.